KR20000016615A - Nonafluoromethoxybutane compositions - Google Patents

Abstract

PURPOSE: Compositions containing nonafluoromethoxybutane are provided which have lower break ability against an ozone layer than conventional compound and are useful as cleaning agents, displacement drying agents, refrigerants, heat transfer media, aerosol propellants, and buffing abrasive agents etc. CONSTITUTION: Compositions of nonafluoromethoxybutane and cyclopentane, nonafluoromethoxybutane and cyclohexane; nonafluoromethoxybutane, cyclopentane and acetone,nonafluoromethoxybutane, cyclohexane and acetone, nonafluoromethoxybutane,trans-1,2-dichloroethylene and cyclopentane; and nonafluoromethoxybutane, trans-1,2-dichloroethylene, cyclopentane and methanol are described. These compositions are useful as cleaning agents, displacement drying agents, refrigerants, heat transfer media, expansion agents for polyolefins and polyurethanes, aerosol propellants, gaseous dielectrics, fire extinguishing agents, power cycle working fluids, polymerization media, particulate removal fluids, carrier fluids, and buffing abrasive agents.

Description

Nonnafluoromethoxybutane Composition

<Related application>

This application claims the benefit of US Provisional Application No. 60/019691, filed June 13, 1996.

Fluorinated hydrocarbons have a variety of uses, such as detergents or refrigerants. Such compounds include trichlorofluoromethane (CFC-11) and 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113).

In recent years, it has been pointed out that the release of certain types of fluorinated hydrocarbon compounds into the atmosphere can adversely affect the stratospheric ozone layer. While this hypothesis is not fully established, there has been a move to regulate the use and production of certain chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) under international agreements.

Thus, there has been a need for the development of new compounds with lower ozone depletion potential than existing compounds, while still having acceptable performance in detergent and cooling applications.

In cooling applications, refrigerant is often lost due to leakage in shaft seals, lake connections, solder joints and broken gaps. In addition, the refrigerant may be released to the atmosphere while being maintained in the cooling device. If the coolant is not a pure component or an azeotrope or similar azeotropic composition, the coolant composition may change when it is leaked or released from the cooling device to the atmosphere so that the coolant has flammable or poor cooling capacity.

Thus, if possible, it is preferred to use azeotropic or analogous azeotrope compositions of a single compound or one or more compounds as the refrigerant.

It is also desirable to find alternatives to CFCs and HCFCs, for example for use as cleaners or solvents for cleaning electrical circuit boards. The electrical elements are soldered to the circuit board by coating the entire circuit portion of the plate with flux and then passing the flux coated plate through the molten solder on the preheater. The flux cleans the conductive metal and promotes solder melting, but leaves a residue on the circuit board that must be removed with the cleaner. Fluorinated hydrocarbons are also useful as detergents in steam degreasing operations and wiping solvent applications.

Preferably, the cleaning agent should have low boiling point, non-volatile, low toxicity and high solvent power so that the flux and flux residues can be removed without damaging the substrate to be cleaned. Also, detergents comprising fluorinated hydrocarbons should preferably be azeotrope or similar azeotrope so that they do not fractionate upon boiling or evaporation. If the cleaner is not an azeotrope or similar azeotrope, the more volatile components of the cleaner are evaporated so that the cleaner is flammable or not so desirable solvent properties, e.g. low rosin flux solvent power and electrical components to be cleaned. It may have a low inertness to. In addition, azeotropic properties are desirable in steam degreasing operations because the cleaners are generally re-distilled and reused for final cleaning. Alternatives may also be useful as wiping solvents.

Alternatives to CFCs and HCFCs are also polymerized as blowing agents in the production of free-standing polyurethanes, phenolic and thermoplastic foams, as propellants in aerosols, as fruits, as gaseous dielectrics, as extinguishing agents, as power cycle working fluids such as heat pumps, As an inert medium for reactions, a liquid for removing particles from a metal surface, a carrier liquid that can be used to place lubricant into a fine film on a metal, buffer abrasive detergent for removing buff abrasives from an abrasive surface such as metal As an alternative desiccant for removing water from gems or metals, as a resist developer in conventional circuit manufacturing methods, including chlorine-based developers, or, for example, with 1,1,1-trichloroethane or trichloroethylene Remover for photoresist when used with the same chlorohydrocarbons Books can be useful.

Therefore, it was found that a composition containing nonafluoromethoxybutane has a low ozone depleting ability and is suitable for a refrigerant, a blowing agent, a cleaning agent, a fruit, and the like.

<Summary of invention>

The present invention relates to a binary composition wherein the first component is nonafluoromethoxybutane and the second component is selected from the group consisting of cyclopentane and cyclohexane.

The present invention also relates to a ternary composition wherein the first component is nonafluoromethoxybutane, the second component is selected from the group consisting of cyclopentane or cyclohexane, and the third component is acetone.

The present invention also relates to a ternary composition wherein the first component is nonafluoromethoxybutane, the second component is trans-1,2-dichloroethylene (trans-1,2-DCE), and the third component is cyclopentane. It is about.

The present invention also relates to a ternary composition wherein the first component is nonafluoromethoxybutane, the second component is trans-1,2-DCE, the third component is cyclopentane, and the fourth component is methanol.

Such compositions include detergents, alternative desiccants, refrigerants, wiping solvents, blowing agents of polyolefins and polyurethanes, aerosol propellants, fruits, gaseous dielectrics, power cycle working fluids, polymerization media, particle removal liquids, extinguishing agents, carrier liquids, and buff abrasives. It is useful as a detergent.

The present invention also relates to an azeotropic or azeotropic composition comprising an effective amount of the above components, forming an azeotropic or azeotropic composition.

The present invention relates to a composition containing nonafluoromethoxybutane. The composition may be nonafluoromethoxybutane and cyclopentane, or nonafluoromethoxybutane and cyclohexane; Or nonafluoromethoxybutane, cyclopentane and acetone, or nonafluoromethoxybutane, cyclohexane and acetone, or nonafluoromethoxybutane, trans-1,2-dichloroethylene and cyclopentane; Or nonafluoromethoxybutane, trans-1,2-dichloroethylene, cyclopentane and methanol. The composition is intended for cleaning agents, wiping solvents, alternative desiccants, refrigerants, fruits, blowing agents of polyolefins and polyurethanes, aerosol propellants, gas phase dielectrics, power cycle working fluids, fire extinguishing agents, polymerizations It is useful as a medium, particle removal liquid, carrier liquid, and buff abrasive detergent.

The present invention relates to binary compositions of nonafluoromethoxybutane (C ₄ F ₉ OCH ₃ ) and cyclopentane or cyclohexane.

The present invention relates to _{ternary compositions} of C ₄ F ₉ OCH ₃ , cyclopentane and acetone, or C ₄ F ₉ OCH ₃ , cyclohexane and acetone, or C ₄ F ₉ OCH ₃ , trans-1,2-DCE and acetone. It is about.

The present invention relates to _{quaternary compositions} of C ₄ F ₉ OCH ₃ , trans-1,2-DCE, cyclopentane and methanol.

1 to 99% by weight of each component of the composition comprises detergents, alternative desiccants, refrigerants, blowing agents of polyolefins and polyurethanes, aerosol propellants, berries, gaseous dielectrics, fire extinguishing agents, power cycle working fluids, polymerization media, particle removal liquids, carriers It can be used as a liquid and a buff abrasive detergent.

In addition, the present invention provides an effective amount of C ₄ F ₉ OCH ₃ and cyclopentane, or an effective amount of C ₄ F ₉ OCH ₃ and cyclohexane to form an azeotrope or similar azeotrope; Or an effective amount of C ₄ F ₉ OCH ₃ , cyclopentane and acetone, or an effective amount of C ₄ F ₉ OCH ₃ , cyclohexane and acetone, or an effective amount of C ₄ F ₉ OCH ₃ , trans-1,2-DCE and cyclopentane ; Or an azeotrope or similar azeotrope of an effective amount of C ₄ F ₉ OCH ₃ , trans-1,2-DCE, cyclopentane and methanol.

In the nonafluoromethoxybutane (C ₄ F ₉ OCH ₃ ) isomer of the present invention, 1,1,1,3,3,3-hexafluoro-2-methoxy-2- has an approximate isomer boiling point of 60 ° C. (Trifluoromethyl) -propane (CH ₃ OC (CF ₃ ) ₃ ), 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane (CH ₃ OCF ₂ CF ₂ CF ₂ CF ₃ ), 1,1,1,2,3,3-hexafluoro-2- (trifluoromethyl) -3-methoxy-propane (CH ₃ OCF ₂ CF (CF ₃ ) ₂ ), and 1,1,1,2,3,3,4,4,4, -nonafluoro-2-methoxybutane (CH ₃ OCF (CF ₃ ) CF ₂ CF ₃ ). Other components of the composition of the present invention include the following.

1.Methanol (CH ₃ OH), boiling point = 65 ° C

2. trans-1,2-dichloroethylene (CHCl = CHCl), boiling point = 48 ° C

3. Acetone (CH ₃ COCH ₃ ), boiling point = 56 ° C

4. Cyclopentane (cyclo (CH ₂ ) ₅ ) boiling point = 41 ° C

5. Cyclohexane (cyclo (CH ₂ ) ₆ ) boiling point = 81 ° C

By "azeotropic" composition is meant a liquid mixture of two or more materials that behave like a single material, which constantly boils. One way to characterize an azeotrope composition is that the liquid and the vapor produced therefrom by partial evaporation or distillation have the same composition, ie a mixture of distillate / reflux with no change in composition. Certain boiling compositions are characterized as azeotrope because they show a maximum or minimum boiling point compared to that of an azeotrope of the same component.

By “anazeotic azeotropic” composition is meant a liquid mixture of two or more materials that behaves like a single material, which is constantly boiling or substantially constant boiling. One way of characterizing the azeotropic azeotrope composition is that the liquid and the vapor produced therefrom by partial evaporation or distillation have substantially the same composition, ie a mixture of distillate / reflux with substantially no change in composition. Another method of characterizing azeotropic azeotropic compositions is that the bubble point vapor pressure and the dew point vapor pressure of the composition at a particular temperature are substantially the same.

In the art, after 50% by weight of the composition is removed by evaporation or boiling, the difference in vapor pressure between the original composition and the composition remaining after 50% by weight of the original composition is removed is less than 10%, if measured in absolute units. The composition is recognized as a pseudo azeotropic mixture. Absolute units are measurements of pressure, for example psia, atmospheric pressure, bar, tor, dyne / cm ² , mmHg, inches of water column and other equivalent terms known in the art. When an azeotrope was present, there was no difference in vapor pressure between the original composition and the composition remaining after 50% by weight of the original composition was removed.

Thus, in the present invention, an effective amount of C ₄ F ₉ OCH ₃ and cyclopentane, wherein a difference in vapor pressure between the original composition and the residual composition is 10% or less even after 50% by weight of the original composition is evaporated or boiled to form a residual composition, or Effective amounts of C ₄ F ₉ OCH ₃ and cyclohexane; Or an effective amount of C ₄ F ₉ OCH ₃ , cyclopentane and acetone, or an effective amount of C ₄ F ₉ OCH ₃ , cyclohexane and acetone, or an effective amount of C ₄ F ₉ OCH ₃ , trans-1,2-DCE and cyclopentane ; Or an effective amount of a composition of C ₄ F ₉ OCH ₃ , trans-1,2-DCE, cyclopentane and methanol.

In an azeotropic composition, at the maximum boiling point azeotrope, it has a boiling point higher than the pure component of the composition at a certain pressure, and at a certain temperature it has a lower vapor pressure than the pure component of the composition, and in a minimum boiling azeotrope the lower boiling point is below the pure component of the composition A range of compositions are typically present around the azeotropic point, having a vapor pressure higher than the pure components of the composition at certain temperatures. The boiling point and vapor pressure above or below the boiling point and vapor pressure of pure components is due to unexpected intermolecular forces between molecules of the composition which can be a combination of repulsive and attractive forces, such as van der Waals forces and hydrogen bonds.

The range of a composition having a maximum or minimum boiling point at a certain pressure, or having a maximum or minimum vapor pressure at a specific temperature is the range of the composition where the vapor pressure changes to less than about 10% by weight when 50% by weight of the composition is evaporated. May or may not be distributed. The range of the composition having the maximum or minimum boiling point at a certain pressure, or having the maximum or minimum vapor pressure at a certain temperature is greater than the range of the composition where the vapor pressure changes to less than about 10% when 50% by weight of the composition is evaporated. Even in a wide range of cases, it is important to note that a refrigerant composition with an intermolecular force may exhibit an unexpected increase in capacity or efficiency for the components of the refrigerant composition, where the unexpected intermolecular forces do not boil substantially constant.

The components of the composition of the present invention have the following vapor pressure.

ingredient 40.0 ℃ 42.8 ℃ Psia 57.8 ℃ Psia 58.0 ℃ Psia C ₄ F ₉ OCH ₃ 7.30 8.10 13.66 13.76 Acetone 8.19 9.11 15.52 15.63 Cyclopentane 10.73 11.82 19.30 19.42 Cyclohexane 3.57 3.99 6.97 7.02 Trans-1,2-DCE 11.27 12.43 20.41 20.54 Methanol 4.91 5.59 10.73 10.82

Azeotropic or similar azeotropic compositions of the present invention that boil substantially constant include the following at the specified temperatures.

Component C ₄ F ₉ OCH ₃ Azeotropic Mixture Temperature (℃) Weight range (wt% / wt%) Preferred range (wt% / wt%) C ₄ F ₉ OCH ₃ / cyclopentane 42.8 29-83 / 17-71 45-83 / 17-55 C ₄ F ₉ OCH ₃ / cyclohexane 57.8 59-99 / 1-41 70-99 / 1-30 C ₄ F ₉ OCH ₃ / cyclopentane / acetone 42.8 1-82 / 17-85 / 1-59 60-82 / 17-30 / 1-30 C ₄ F ₉ OCH ₃ / cyclohexane / acetone 58.0 1-98 / 1-60 / 1-98 60-99 / 1-40 / 1-40 C ₄ F ₉ OCH ₃ / trans-1,2-DCE / cyclopentane 40.0 40-75 / 1-59 / 1-59 50-75 / 1-40 / 1-30 C ₄ F ₉ OCH ₃ / trans-1,2-DCE / cyclopentane / methanol 40.0 40-70 / 15-50 / 1-25 / 1-10 40-60 / 20-40 / 5-20 / 1-8

For the purposes of the present invention, an "effective amount" is defined as the amount of each component of the composition of the present invention and, when mixed, forms an azeotrope or pseudoazeotropic composition. This definition includes the amount of each component that can vary depending on the pressure applied to the composition, as long as the azeotropic or analogous azeotrope composition has different boiling points but is continuously present at different pressures.

Thus, effective amounts include amounts that can be expressed as weight percent of each component of a composition of the present invention that forms an azeotrope or similar azeotrope composition at temperatures or pressures not described herein.

For the purposes of the present invention, azeotropy or constant boiling means essentially azeotropic mixtures or essentially constant boiling. In other words, within the meaning of this term is not only the true azeotrope mentioned above, but also other compositions comprising the same components in different proportions, which are true azeotropees at different temperatures and pressures, and parts of the same azeotrope system and similar azeotropees. Equivalent compositions having properties are included. As is known in the art, there is a range of compositions that contain the same components as the azeotropic mixture, which is essentially equivalent to properties for cooling and other uses, as well as not being separated or fractionated at constant boiling properties or boiling. It will tend to be essentially equivalent in nature to a true azeotrope composition.

Certain boiling mixtures that may vary depending on the selection conditions can be characterized by the following areas.

* Since the term "azeotropic mixture" is simultaneously limited and limiting, the composition can be defined as an azeotrope of A, B, C (and D ...), A of the composition to be a constant boiling composition of the only composition, Requires an effective amount of B, C (and D ...).

As is known in the art, the composition of a given azeotrope at different pressures will change at least to some extent and the change in pressure will change the boiling point temperature at least to some extent. Thus, azeotropic mixtures of A, B, C (and D ...) show a unique type of relationship but are of varying composition depending on temperature and / or pressure. Thus, the composition range is often defined and used as an azeotrope rather than a fixed composition.

The composition may be defined as a specific weight percent relationship or molar percent relationship of A, B, C (and D ...), where said specific value represents only one specific relationship and is in fact A, B, C (and D). It is known that a series of relationships represented by ...) exist substantially for a given azeotropic mixture which is changed by the influence of pressure.

Azeotropic mixtures of A, B, C (and D ...) define the composition as an azeotrope which is characterized by the boiling point at a given pressure and are as accurate as the analytical device without unambiguously limiting the scope of the invention. It can be characterized by characterizing it with a certain number of compositions that are limited by what is present.

The azeotrope or similar azeotrope composition of the present invention may be prepared by any conventional method, including mixing the desired amount. The preferred method is to weigh the desired amount of ingredients and then mix them in a suitable container.

Specific examples illustrating the invention are described below. All percentages are expressed in weight unless otherwise indicated. This embodiment is illustrative only and should not be construed as limiting the scope of the invention in any way. It is believed that all isomers of C ₄ F ₉ OCH ₃ will give similar results.

<Example 1>

Phase research

Phase studies show that the following components are substantially azeotrope at atmospheric pressure.

Vapor pressure Composition weight% psia kPa Temperature (℃) C ₄ F ₉ OCH ₃ / cyclopentane 57.1 / 42.9 14.68 101 42.8 C ₄ F ₉ OCH ₃ / cyclohexane 88.4 / 11.6 14.67 101 57.8

<Example 2>

Effect of Steam Leakage on Steam Pressure

The vessel was filled with the initial composition at the specified temperature and the vapor pressure of the composition was measured. While maintaining the temperature constant at the specified temperature, the composition was allowed to leak out of the container until 50% by weight of the initial composition was removed, at which time the vapor pressure of the composition remaining in the container was measured. The results are summarized below.

The results of this example show that the composition is an azeotrope or similar azeotrope because the vapor pressure of the remaining composition when the 50% by weight of the original composition is removed is less than about 10% by weight of the vapor pressure of the original composition at 25 ° C.

<Example 3>

Effect of Steam Leak at 25 ° C

Leak tests were performed on the compositions of C ₄ F ₉ OCH ₃ and cyclohexane at 25 ° C. The results were as follows.

The results showed that the compositions of C ₄ F ₉ OCH ₃ and cyclohexane differed at different temperatures from the azeotrope or similar azeotrope, but the weight percent of the components changed as the temperature changed.

<Example 4>

Effect of C ₄ F ₉ OCH ₃ Isomers on Vapor Leakage

The vessel was filled with the initial composition at the specified temperature and the vapor pressure of the composition was measured. While keeping the temperature constant at the specified temperature, the composition was allowed to leak from the container until 50% by weight of the initial composition was removed, at which time the vapor pressure of the composition remaining in the container was measured. The results are summarized below.

The results showed that different isomers of C ₄ F ₉ OCH ₃ provide equivalent azeotropic points and leak performance.

<Example 5>

Refrigerant Performance

The following table shows the performance of various refrigerants. The data is based on the following conditions.

Evaporator Temperature: 40.0 ° F (4.4 ° C)

Condenser temperature: 110.0 ° F (43.3 ° C)

Lower Cooling: 10.0 ° F (5.6 ° C)

Reducing gas temperature: 75.0 ° F. (23.8 ° C.)

Compressor efficiency: 70%

The cooling capacity is based on a compressor with a fixed replacement capacity of 3.5 feet ³ / min and a volume efficiency of 70%.

Capacity means the change in enthalpy of the refrigerant in the evaporator per pound of refrigerant circulated, ie the heat removed by the refrigerant in the evaporator per hour. The coefficient of performance (COP) refers to the ratio of capacity to compressor operation. This is a measure of refrigerant energy efficiency.

<Example 6>

Several cross-sectional circuit boards were coated with Alpha 611F RMA rosin flux and then heated to 165 ° C. for 2 minutes to activate. The plates were defluxed in boiling solutions of 55.0 wt% C ₄ F ₉ OCH ₃ , 25.0 wt% trans-dichloroethylene, 14.0 wt% cyclopentane and 6.0 wt% methanol. The cleaning cycle consists of soaking in boiling solution for 2 minutes and then leaving it in steam for 30 seconds. After cleaning, the plate had no residue left that could be visualized.

<Example 7>

Chamber deposit samples containing polymers of carbon, fluorine, hydrogen and possibly other atoms were immersed in a solution of 85.0 wt% C ₄ F ₉ OCH ₃ , 5.0 wt% cyclohexane and 10.0 wt% acetone for 1 hour. Solid deposits were softened to gel. The softened deposits were then mechanically removed to keep the surface clean.

The novel compounds of the present invention, including azeotrope compositions or similar azeotrope compositions, can be used, for example, as cleaning agents for cleaning electrical circuit boards. It is preferred that the cleaner is an azeotrope or similar azeotrope, because in steam degreasing operations the cleaner is generally re-distilled and reused for final cleaning. The novel composition can also be used as an alternative desiccant and wiping solvent for removing water from the surface.

The novel compositions of the present invention, including azeotropic or analogous azeotropic compositions, can act by cooling by condensing the composition and then evaporating the mantle near the object to be cooled. The novel composition can also generate heat by condensing the refrigerant near the object to be heated and then evaporating the refrigerant.

The novel compositions of the present invention are particularly suitable for replacing compounds that may affect the ozone layer, including R-113 and R-11.

In addition to detergent and refrigerant uses, the constant boiling or substantially constant boiling new compositions of the present invention are also useful as aerosol propellants, fruit, gaseous dielectrics, extinguishing agents, blowing agents of polyolefins and polyurethanes, and power cycle working fluids.

<Additional compound>

Other components such as aliphatic hydrocarbons having a boiling point of 0 to 100 ° C., hydrofluorocarbonalkanes having a boiling point of 0 to 100 ° C., hydrofluoropropanes having a boiling point of 0 to 100 ° C., hydrocarbons having a boiling point of 0 to 100 ° C. Ester, hydrochlorofluorocarbons having a boiling point of 0 to 100 ° C., hydrofluorocarbons having a boiling point of 0 to 100 ° C., hydrochlorocarbons having a boiling point of 0 to 100 ° C., chlorocarbons and perfluorinated compounds are constantly boiling It can be added to the azeotrope or similar azeotrope described above without substantially changing the properties of the composition, including the properties to be made.

Additives such as lubricants, corrosion inhibitors, surfactants, stabilizers, dyes and other suitable materials may be added to the novel compositions of the present invention for various purposes, provided they do not adversely affect the composition for the intended use. Preferred lubricants include esters having a molecular weight greater than 250.

Claims (20)

Nonafluoromethoxybutane and cyclopentane or nonafluoromethoxybutane and cyclohexane; Or nonafluoromethoxybutane, cyclopentane and acetone, or nonafluoromethoxybutane, cyclohexane and acetone, or nonafluoromethoxybutane, trans-1,2-dichloroethylene and cyclopentane; Or nonafluoromethoxybutane, trans-1,2-dichloroethylene, cyclopentane and methanol. Nonafluoromethoxybutane and cyclopentane or nonafluoromethoxybutane and cyclohexane; Or nonafluoromethoxybutane, cyclopentane and acetone, or nonafluoromethoxybutane, cyclohexane and acetone, or nonafluoromethoxybutane, trans-1,2-dichloroethylene and cyclopentane; Or an azeotrope or similar azeotrope composition comprising an effective amount of nonafluoromethoxybutane, trans-1,2-dichloroethylene, cyclopentane and methanol. The composition of claim 2, wherein the composition comprises 29 to 83 weight percent nonafluoromethoxybutane and 17 to 71 weight percent cyclopentane; Alternatively 59 to 99% by weight of nonafluoromethoxybutane and 1 to 41% by weight of cyclohexane; Or 1 to 82% by weight of nonafluoromethoxybutane, 17 to 85% by weight of cyclopentane and 1 to 59% by weight of acetone; Or 1 to 98% by weight of nonafluoromethoxybutane, 1 to 60% by weight of cyclohexane and 1 to 98% by weight of acetone; Or 40 to 75 weight percent of nonafluoromethoxybutane, 1 to 59 weight percent of trans-1,2-dichloroethylene and 1 to 59 weight percent of cyclopentane; Or azeotropic or similar azeotropic composition comprising 40 to 70% by weight of nonafluoromethoxybutane, 15 to 50% by weight of trans-1,2-dichloroethylene, 1 to 25% by weight of cyclopentane and 1 to 10% by weight of methanol. The composition of claim 2, wherein the composition comprises 45 to 83 weight percent nonafluoromethoxybutane and 17 to 55 weight percent cyclopentane; Or 70 to 99% by weight of nonafluoromethoxybutane and 1 to 30% by weight of cyclohexane; Or 60 to 82% by weight of nonafluoromethoxybutane, 17 to 30% by weight of cyclopentane and 1 to 30% by weight of acetone; Or 60 to 99% by weight of nonafluoromethoxybutane, 1 to 40% by weight of cyclohexane and 1 to 40% by weight of acetone; Or 50 to 75% by weight of nonafluoromethoxybutane, 1 to 40% by weight of trans-1,2-dichloroethylene and 1 to 30% by weight of cyclopentane; Or azeotropic or similar azeotropic composition comprising 40 to 60% by weight of nonafluoromethoxybutane, 20 to 40% by weight of trans-1,2-dichloroethylene, 5 to 20% by weight of cyclopentane and 1 to 8% by weight of methanol. After condensing the composition of claim 1, comprising evaporating said composition near the object to be cooled. After condensing the composition of claim 2, the method comprises evaporating the composition near an object to be cooled. After condensing the composition of claim 3, evaporating said composition near an object to be cooled. A method of cooling comprising evaporating the composition near an object to be cooled after condensing the composition of claim 4. A method of spraying a fluid comprising using the composition of claim 1 as an aerosol propellant. A method of spraying a fluid comprising using the composition of claim 2 as an aerosol propellant. A method of spraying a fluid comprising using the composition of claim 3 as an aerosol propellant. A method of spraying a fluid comprising using the composition of claim 4 as an aerosol propellant. A method of cleaning a solid surface, comprising treating the solid surface with the composition of claim 1. A method of cleaning a solid surface, comprising treating the solid surface with the composition of claim 2. A method of cleaning a solid surface, comprising treating the solid surface with the composition of claim 3. A method of cleaning a solid surface, comprising treating the solid surface with the composition of claim 4. A method of heat transfer from a heat source to a heat sink using the composition of claim 1. A method of heat transfer from a heat source to a heat sink using the composition of claim 2. A method of heat transfer from a heat source to a heat sink using the composition of claim 3. A method of heat transfer from a heat source to a heat sink using the composition of claim 4.